Headstrong may refer to:

• Headstrong (band), a Canadian rap rock band
  • Headstrong (Headstrong album), the self-titled 2002 debut album by Headstrong
• Headstrong (Ashley Tisdale album), 2007, or the title track
• "Headstrong", a song by Earshot from the 2002 album Letting Go
• "Headstrong" (Trapt song), 2002
• Headstrong (play), a stage play by Patrick Link
• Operation Headstrong (2003–2004), involving the training of Afghan commandos by British special forces
• Headstrong, an alias used by electronic music producer Geert Huinink
• Headstrong (Transformers), a character in Transformers fiction

• King Louis X of France (1289-1316), called the Headstrong
• Headstrong Club, an 18th-century English debating society